Ammonium Chloride → 1-(2,6-Dichloropyridin-4-YL)ethanone

HRID 1187692Notes

Reaction equation

HRID 1187692 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:14])[N:13]=1)[C:5](N(OC)C)=[O:6].O1CCC[CH2:16]1.C[Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH3:16])[CH:11]=[C:12]([Cl:14])[N:13]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 219482182,6-Dichloro-N-methoxy-N-methylisonicotinamideHCID 178420675HCID 178420675, compound

Product 1

HCID 221194461-(2,6-Dichloropyridin-4-YL)ethanone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

490 mg of 2,6-dichloro-N-methoxy-N-methyl isonicotinamide was dissolved in tetrahydrofuran, 2.1 ml of 3M methyl magnesium bromide tetrahydrofuran solution was added dropwise at 0° C., and the mixture was stirred at 0° C. for 1 hour. To the reaction solution was added ammonium chloride aqueous solution, and the mixture was diluted with ethyl acetate. The mixture was washed with brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 325 mg of the objective compound.

Workup

  1. washThe mixture was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4ba0665576fc45e789e091e37966bd77
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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